How an Intelligence Officer Used Monopoly to Free POWs

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What got Christopher Clayton Hutton his job as an intelligence officer at MI9 wasn’t anything on his professional resume. His career as a journalist, his work in Hollywood publicity departments, and his stint as a pilot in the Royal Air Force during the First World War mattered little to the War Office when he applied in 1939. “My passport to the whole curious business,” he recounted 22 years later in his autobiography, Official Secret, “had been a casual reference to my thwarted efforts to get the better of Harry Houdini, the world’s greatest escapologist.”

During his interview, Hutton—or Clutty, as he was called—recounted to Major J.H. Russell how, on April 29, 1915, he had written to the legendary showman, challenging him to escape from a box built on stage, in full view of the audience, by the master carpenter of his father’s timber mill company. “You enter immediately,” Hutton wrote, “wenail down the lid, securely rope up the box, and defy you to escape without demolishing same.”

Houdini accepted, with one condition: that he be allowed to visit the timber mill and meet the carpenter. Hutton, then just 20, arranged the meeting—not realizing, until much later, that Houdini had used the time to bribe the woodworker. In exchange for a mere £3 (less than $5), the carpenter agreed to build the box in such a way that, once Houdini was inside and the box was concealed behind a curtain, it would be easy for the famous escape artist to push one end off using just his feet, then nail it back on properly while the orchestra at the performance played especially loudly.

Though he’d always been interested in show business, Hutton told Russell that the Houdini incident marked the beginning of an obsession with magic. “Magicians, illusionists, escapeologists in particular—they all fascinate me,” Hutton said.

“You may be the very man we want,” Russell replied. “We’re looking for a showman with an interest in escapology.” And just like that, Hutton was hired.

Hutton’s job, he learned that day, would be to build and conceal tools that would allow Allied prisoners of war to escape German POW camps. Over the course of World War II, 232,000 Western Allies (and 5.7 million Soviet soldiers) were imprisoned in the camps, most of which were located in Eastern Germany and Austria, making for a long and difficult route back home. The prisoners, Hutton’s superior told him, were being instructed to try to escape, with the hope that they would be able to divert German soldiers from the front. Clutty was given the rank of lieutenant and told to get to work.

It quickly became clear that Clutty had no respect for rules or boundaries. He often employed unorthodox methods, and stepped on plenty of toes, to get things done. “This officer is eccentric,” his commanding officer wrote to a provost marshal. “He cannot be expected to comply with ordinary service discipline, but he is far too valuable for his services to be lost to this department.” Hutton and his team regularly churned out impressive devices to aid POWs in their escape attempts, including flying boots with hollow heels that held knives, maps, a compass, and a file—and could also be transformed into civilian shoes; a telescope disguised as a cigarette holder; and compasses so tiny they could be hidden on the backs of buttons.

But as ingenious as Hutton’s concealments were, the Germans inevitably figured them out. All of them, that is, but one. This particular scheme that Clutty had hatched wouldn’t come to light until the documents were declassified four decades after the end of the war: With the help of a Leeds-based manufacturing company, Hutton hid escape kits for POWs in unassuming, ordinary-looking Monopoly games.

MAPS AND MONOPOLY

Monopoly first made its way to the UK in 1935, just a few months after Parker Brothers purchased it from Charles Darrow. Not long after, the company shipped the game overseas to its U.K. partners, John Waddington Limited, a printing and packaging company that was beginning to make the move into games. “The Waddingtons were so taken by Monopoly that they immediately licensed it in December 1935,” Philip Orbanes, a Monopoly historian at Parker Brothers and author of three books about the game, tells mental_floss. “They adapted it to the market by changing the street names to appropriate streets in London.” The game, released in 1936, was an immediate hit in England.

In its original role as a printing company, Waddingtons was responsible for creating the silk play bills that were presented to the Royal Family at command performances. This had required the company to perfect the process of printing on silk, which its workers had accomplished by stretching the material and adding a gummy substance called pectin to the ink to keep it from running. The innovation made the printing of highly detailed silk escape maps—which didn’t rustle like paper maps, were impervious to dirt and water, and didn’t distort—possible, and the company was already making thousands for MI9, which were sewn into airmen’s uniforms. It was a perfect solution if an airman somehow managed to evade capture. But what about the men who ended up in POW camps?


From the collection of Philip E. Orbanes. Click to enlarge.

Clutty knew that games were allowed into camps; the Germans believed they provided a diversion for POWs whose main activity was trying to figure out how they could escape. And then inspiration struck: Most of his devices could only conceal one tiny tool, but a game with a large board could hide a silk map, a small compass, a Gigli saw, and a file. Waddingtons made silk maps—and Monopoly. The game was large enough for what he wanted, and the fake money could conceal the real money that POWs on the run would need. It was perfect for Hutton’s all-in-one escape kit.

On March 26, 1941, Hutton discussed the matter with the company's chairman, Victor Watson, then followed up with a letter that same day, which read, in part:

Dear Mr. Watson,

Reference our conversation today. I am sending you, under separate cover, as many maps as I have in stock of the following:
Norway and Sweden
Germany
Italy

I shall be glad if you will make up games on the lines discussed today containing the maps as follows:

One game must contain Norway, Sweden, and Germany.
One game must contain N. France, Germany, and frontiers.
One game must contain Italy.

I am also sending you a packet of small metal instruments. I should be glad if in each game you could manage to secrete one of these.

I want as varied an assortment containing these articles as possible. You had then better send me 100/200 games on the straight.

In those that are faked, you must give me some distinguishing clue and also state what they contain.

Waddingtons put just a few workers on the project, secluding them in a small room, where they used cookie cutter-like dies to punch compartments exactly the size of the items into the Monopoly boards—which were then an eighth of an inch thick, compared to today’s twelfth of an inch—before gluing the game board decal over it. When their job was done, the board was indistinguishable from one a regular citizen might buy in a store.


Courtesy of Philip E. Orbanes. Click to enlarge.

GETTING THE GAMES INTO THE CAMPS

After designing his ingenious escape aids, Clutty’s greatest challenge was figuring out how to actually get them into the camps. He couldn’t use Red Cross packages, and monthly personal packages sent to POWs by family and friends were out, too. “I had no doubt that if the Germans discovered an illegal item in a ‘family’ parcel, they would have no compunction about withdrawing the privilege altogether,” Clutty wrote in Open Secret.

But Hutton knew that hundreds of organizations were sending care packages to POWs, and he decided to use that to his advantage. “We would hide our escape aids in parcels containing games, sports equipment, musical instruments, books, and articles of clothing,” he wrote. “We knew that these voluntary gifts, designed for the comfort and entertainment of the prisoners, were flooding the camps from hundreds of sources … There was no valid reason why we should not take cover behind this multiplicity of well-wishers.”

He and his team created a bunch of bogus organizations using the addresses of blitzed buildings. A printer made letterheads for the organizations “littered with quotations that we hoped would act both as clues and as an inspiration to the prisoners,” Clutty wrote. “One obvious quotation was from St. Matthew, Chapter 7: ‘Ask and it shall be given you; seek and ye shall find; knock and it shall be opened unto you.’” To make their packages as authentic looking as possible, the team wrapped the parcels that supposedly came from Liverpool organizations, for example, in sheets from the Liverpool Echo.

To see if their packages were getting through, Hutton and his team enclosed “a printed card of acknowledgement on which the contents were enumerated. All the prisoner had to do was to tick off each article as received and return the card,” which was slightly bigger than the one used by the Red Cross, allowing for easy sorting by the censors. After sending out the first batch—which contained no contraband—the team waited and waited to receive cards. “We grew more and more depressed,” Hutton wrote, “telling ourselves gloomily that the Jerries had confiscated the lot and we should hear no more about the matter.”

But then, three months after they’d sent their packages, a card came in—then another, and another. The packages had gotten through! It was time to send through a batch that wasn’t entirely legitimate. “These plans of mine were greeted on all sides with complete skepticism,” Hutton wrote. “Even Major Crockatt said to me as the first 13 loaded parcels were sent, ‘They will never get through in 100 years.’” But Crockatt was wrong. Everything, even the fake material, had been delivered: “We had our entree into the camps.”

SENDING A MESSAGE

Getting the games into the camps was just one part of getting the tools to the POWs. Clutty also had to make sure that the prisoners knew what they were receiving. Clever messages that hinted at what was hidden inside the packages weren't enough; Clutty decided to train at least two members of every Air Force squadron in the art of sending hidden messages concealed in ordinary looking letters addressed to Mom and Dad.

When the trained men mailed letters back to the UK, those letters were intercepted and given to intelligence officers, who steamed them open and took a look at the date. “If it was written out, M-A-Y 3rd, the letter was simply resealed, and it went to whatever relative it was addressed to,” Orbanes says. “But if the letter’s date was numerical—three slash five slash '43—that said ‘there’s a message in this letter.’” The intelligence officer would then multiply the number of letters in the first two words to determine how many words were in the message. If the first two words were “how nice,” for example, then the officer would multiply three by four to get 12 words. “Then,” Orbanes says, “there was a technique by which he could pick out the words in the letter and write out the message.”

This allowed intelligence officers and POWs to communicate back and forth. POWs reported on conditions in the camp, and what they might need to escape—and intelligence officers let them know when special packages were coming their way. “The code user in the camp would eventually get a letter back from ‘Mom or Dad’ that would contain a secret message, and it would tell them when to expect the shipment and what the parcels might look like,” Orbanes says. The contents of Clutty's escape kits could be modified based on requests from code users.


Courtesy of Philip E. Orbanes. Click to enlarge.

Because keeping the secret of how escape tools were getting into the camps was paramount, only a few men ever knew how it was happening. Each POW camp had an escape committee that would receive the items, destroy the method of delivery by burning it in the barracks stove, and hide the tools away in false walls. “Ninety-nine percent of all the POWs had no idea of how the tools were getting into the camps,” Orbanes says. “If you and your buddies had a plan for an escape, you would go to the escape committee and present your idea. And if it was approved, they would issue you the tools you needed. So the POWs got what they needed to effectuate their plan, but they never knew how the tools got into the camp.”

THE AMERICAN EFFORT

When the United States entered the war, after the Japanese attacked Pearl Harbor on December 7, 1941, Hutton was tasked with training his American counterpart, Captain Robley Winfrey, in the art of concealing escape tools in ordinary looking stuff. Winfrey, a civil engineering professor at Iowa State, took a leave of absence to join the Army when the U.S. entered the war; he set up a large, secret operation, Military Intelligence Services—Escape and Evasion Section (MIS-X), on the grounds of Mount Vernon in Virginia. Winfrey came up with a number of ideas to supplement Hutton’s, and it wasn’t long before MIS-X was sending out Monopoly boards loaded with escape tools, too.

But Winfrey’s operation differed from Hutton’s in one very important way: He didn’t have a factory that was making complete escape kit boards for him. Instead, he had to send MIS-X staffers in civilian clothes to stores to buy the games. “They would bring the games back to their facility and steam off the gameboard labels,” Orbanes says. “Then they would cut the compartments in, put in the particular escape tools that they wanted inside that game, and then re-apply the label—they actually had to reverse engineer the glue that Parker used.” Not even Parker Brothers knew their boards were being doctored.

GAME OVER

The Germans had discovered a number of Clutty and Winfrey’s concealments, so the duo always had to be one step ahead of the enemy. When the Germans realized that the cribbage boards prisoners were receiving actually contained radio parts, Winfrey began hiding the parts in the cores of baseballs; it took four baseballs to conceal enough parts to build one radio. Table tennis, Snakes & Ladders, chess sets, and playing cards were used to get escape tools and maps into POW camps.

When the war ended in September 1945, there was just one escape kit the Germans hadn’t discovered: Monopoly. None of the modified boards survived—the POWs had to destroy the boards that came into the camps, and MI9 and MIS-X destroyed whatever was left at the end of the war—and the role the game played wouldn’t be revealed until 1985, when British intelligence declassified documents related to Clutty’s work in MI9. MIS-X’s use of the game wasn’t revealed until 1990, when a member of that team was granted permission to tell his story.

According to Orbanes, at least 744 airmen escaped with aids created by Hutton and Winfrey. One of them was an American officer, Lieutenant David Bowling, who was a prisoner at Stalag Luft III, 100 miles southeast of Berlin. In late 1943, he responded to a commanding officer’s request for a solo escape attempt—which, if Bowling was recaptured, was punishable by death. “Leaders inside the camp had learned that the SS was attempting to wrest control of POW camps from the Luftwaffe,” Orbanes says. “With the war turning against the Germans, the SS proposed executing all POWs in order to free the security forces to bolster the front lines. This possibility had to be communicated quickly to Allied Command in England.”

Bowling spoke German well, and was issued civilian clothing, a forged ID, and a train schedule. He also traveled with German money, a silk map, a tiny compass, wire cutters, and a Gigli saw, which most likely came from a Monopoly game.

A few nights after getting the orders, Bowling waited until lights out at 10 p.m., crawled to the wire, and cut his way through, making his way to Sagan, about 10 miles away, where, the next morning, he boarded a train heading toward Switzerland, according to his map. “For days, Bowling guided his movements by his compass and map,” Orbanes says. “At times, he had to cut through fence wire to avoid walking across fields and remain hidden in woods.” Bowling eventually made it to Zurich and relayed the urgent message.

Were there more attempts like Bowling’s? Most definitely. But we’ll never know for sure just how many—most of the records, British and American, were destroyed just after the war ended. Says Orbanes, “These were better kept secrets than the Manhattan Project.”

15 Gripping Facts About Galileo

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Getty Images

Albert Einstein once said that the work of Galileo Galilei “marks the real beginning of physics.” And astronomy, too: Galileo was the first to aim a telescope at the night sky, and his discoveries changed our picture of the cosmos. Here are 15 things that you might not know about the father of modern science, who was born February 15, 1564.

1. There's a reason why Galileo Galilei's first name echoes his last name.

You may have noticed that Galileo Galilei’s given name is a virtual carbon-copy of his family name. In her book Galileo’s Daughter, Dava Sobel explains that in Galileo’s native Tuscany, it was customary to give the first-born son a Christian name based on the family name (in this case, Galilei). Over the years, the first name won out, and we’ve come to remember the scientist simply as “Galileo.”

2. Galileo Galilei probably never dropped anything off the leaning tower of Pisa. 

With its convenient “tilt,” the famous tower in Pisa, where Galileo spent the early part of his career, would have been the perfect place to test his theories of motion, and of falling bodies in particular. Did Galileo drop objects of different weights, to see which would strike the ground first? Unfortunately, we have only one written account of Galileo performing such an experiment, written many years later. Historians suspect that if Galileo taken part in such a grand spectacle, there would be more documentation. (However, physicist Steve Shore did perform the experiment at the tower in 2009; I videotaped it and put the results on YouTube.)

3. Galileo taught his students how to cast horoscopes.

It’s awkward to think of the father of modern science mucking about with astrology. But we should keep two things in mind: First, as historians remind us, it’s problematic to judge past events by today’s standards. We know that astrology is bunk, but in Galileo’s time, astrology was only just beginning to disentangle from astronomy. Besides, Galileo wasn’t rich: A professor who could teach astrological methods would be in greater demand than one who couldn’t.

4. Galileo didn't like being told what to do.

Maybe you already knew that, based on his eventual kerfuffle with the Roman Catholic Church. But even as a young professor at the University of Pisa, Galileo had a reputation for rocking the boat. The university’s rules demanded that he wear his formal robes at all times. He refused—he thought it was pretentious and considered the bulky gown a nuisance. So the university docked his pay.

5. Galileo Galilei didn't invent the telescope.

We’re not sure who did, although a Dutch spectacle-maker named Hans Lipperhey often gets the credit (he applied for a patent in the fall of 1608). Within a year, Galileo Galilei obtained one of these Dutch instruments and quickly improved the design. Soon, he had a telescope that could magnify 20 or even 30 times. As historian of science Owen Gingerich has put it, Galileo had managed “to turn a popular carnival toy into a scientific instrument.”

6. A king leaned on Galileo to name planets after him.

Galileo rose to fame in 1610 after discovering, among other things, that the planet Jupiter is accompanied by four little moons, never previously observed (and invisible without telescopic aid). Galileo dubbed them the “Medicean stars” after his patron, Cosimo II of the Medici family, who ruled over Tuscany. The news spread quickly; soon the king of France was asking Galileo if he might discover some more worlds and name them after him.

7. Galileo didn't have trouble with the church for the first two-thirds of his life.

In fact, the Vatican was keen on acquiring astronomical knowledge, because such data was vital for working out the dates of Easter and other holidays. In 1611, when Galileo visited Rome to show off his telescope to the Jesuit astronomers there, he was welcomed with open arms. The future Pope Urban VIII had one of Galileo’s essays read to him over dinner and even wrote a poem in praise of the scientist. It was only later, when a few disgruntled conservative professors began to speak out against Galileo, that things started to go downhill. It got even worse in 1616, when the Vatican officially denounced the heliocentric (sun-centered) system described by Copernicus, which all of Galileo’s observations seemed to support. And yet, the problem wasn’t Copernicanism. More vexing was the notion of a moving Earth, which seemed to contradict certain verses in the Bible.

8. Galileo probably could have earned a living as an artist.

We think of Galileo as a scientist, but his interests—and talents—straddled several disciplines. Galileo could draw and paint as well as many of his countrymen and was a master of perspective—a skill that no doubt helped him interpret the sights revealed by his telescope. His drawings of the Moon are particularly striking. As the art professor Samuel Edgerton has put it, Galileo’s work shows “the deft brushstrokes of a practiced watercolorist”; his images have “an attractive, soft, and luminescent quality.” Edgerton writes of Galileo’s “almost impressionistic technique” more than 250 years before Impressionism developed.

10. Galileo wrote about relativity long before Einstein.

He didn’t write about exactly the same sort of relativity that Einstein did. But Galileo understood very clearly that motion is relative—that is, that your perception of motion has to do with your own movement as well as that of the object you’re looking at. In fact, if you were locked inside a windowless cabin on a ship, you’d have no way of knowing if the ship was motionless, or moving at a steady speed. More than 250 years later, these ideas would be fodder for the mind of the young Einstein.

10. Galileo never married, but that doesn't mean he was alone.

Galileo was very close with a beautiful woman from Venice named Marina Gamba; together, they had two daughters and a son. And yet, they never married, nor even shared a home. Why not? As Dava Sobel notes, it was traditional for scholars in those days to remain single; perceived class difference may also have played a role.

11. You can listen to music composed by Galileo's dad.

Galileo’s father, Vincenzo, was a professional musician and music teacher. Several of his compositions have survived, and you can find modern recordings of them on CD (like this one). The young Galileo learned to play the lute by his father’s side; in time he became an accomplished musician in his own right. His music sense may have aided in his scientific work. With no precision clocks, Galileo was still able to time rolling and falling objects to within mere fractions of a second.

12. His discoveries may have influenced a scene in one of Shakespeare's late plays.

An amusing point of trivia is that Galileo and Shakespeare were born in the same year (1564). By the time Galileo aimed his telescope at the night sky, however, the English playwright was nearing the end of his career. But he wasn’t quite ready to put down the quill: His late play Cymbeline contains what may be an allusion to one of Galileo’s greatest discoveries—the four moons circling Jupiter. In the play’s final act, the god Jupiter descends from the heavens, and four ghosts dance around him in a circle. It could be a coincidence—or, as I suggest in my book The Science of Shakespeare, it could hint at the Bard's awareness of one of the great scientific discoveries of the time.

13. Galileo had some big-name visitors while under house arrest.

Charged with “vehement suspicion of heresy,” Galileo spent the final eight years of his life under house arrest in his villa outside of Florence. But he was able to keep writing and, apparently, to receive visitors, among them two famous Englishmen: the poet John Milton and the philosopher Thomas Hobbes.

14. Galileo's bones have not rested in peace.

When Galileo died in 1642, the Vatican refused to allow his remains to be buried alongside family members in Florence’s Santa Croce Basilica; instead, his bones were relegated to a side chapel. A century later, however, his reputation had improved, and his remains (minus a few fingers) were transferred to their present location, beneath a grand tomb in the basilica’s main chapel. Michelangelo is nearby.

15. Galileo might not have been thrilled with the Vatican's 1992 "apology."

In 1992, under Pope John Paul II, the Vatican issued an official statement admitting that it was wrong to have persecuted Galileo. But the statement seemed to place most of the blame on the clerks and theological advisers who worked on Galileo’s case—and not on Pope Urban VIII, who presided over the trial. Nor was the charge of heresy overturned.

Additional sources: The Discoveries and Opinions of Galileo; Galileo's Daughter; The Cambridge Companion to Galileo.

8 Daring Female Entrepreneurs From History

An assortment of Madam C.J. Walker products
An assortment of Madam C.J. Walker products
FA2010, Wikimedia Commons // Public Domain

In the past 20 years, the number of women-owned businesses has risen 114 percent. But female entrepreneurship isn't just a hallmark of the modern era: Since as early as the 17th century, women have been forging their own paths in a variety of trades. From merchants to ironmasters to dressmakers, these historic women shattered glass ceilings and broke stereotypes to rise to the top of their industries.

1. Margaret Hardenbroeck

When 22-year-old Margaret Hardenbroeck arrived in New Amsterdam (later New York) from the Netherlands in 1659, she was ambitious and ready to work. She already had a job lined up—collecting debts for a cousin's business. She continued to work even after she married the wealthy merchant Pieter de Vries, this time as a business agent for several Dutch merchants. She sold small goods like cooking oil to the colonists, and bought furs to send to Holland.

When Peter died in 1661, Hardenbroeck inherited his estate and took over his business. She expanded her fur shipping operations in Holland, trading the furs for merchandise to sell back in the colonies. For the Dutch, it was not wholly unusual for women to run businesses on equal footing with men; in New Amsterdam, they sometimes called themselves she-merchants. Hardenbroeck would become the most successful and wealthiest she-merchant in the colony.

Eventually, she was able to purchase her own ship, the King Charles, and accumulated real estate holdings throughout the colonies. Ever the savvy businesswoman, Hardenbroeck ensured that her wealth, properties, and independence were protected when she married her second husband, Frederick Philipse, by choosing an usus marriage under Dutch law. That meant she rejected marital guardianship of her husband and communal property, retaining all that was hers prior to marriage. When Hardenbroeck died in 1691, she was the wealthiest woman in New York.

2. Rebecca Lukens

Printed picture of Rebecca Lukens, c. 1820
Rebecca Lukens circa 1820
Hagley Museum Collection, Wikimedia // Public Domain

In 1825, 31-year-old Rebecca Lukens found herself a widow and the new owner of Brandywine Iron Works and Nail Factory. The Pennsylvania-based company had been started by Lukens’s father Isaac Pennock in 1810, leased to her husband Charles, and ultimately left to her after both men died only a year apart. As uncommon as it was at the time for a women to be an ironmaster, and despite objections from her own family, Lukens took over and led the company into a new era of innovation and industry.

Under her husband’s leadership, Brandywine Iron Works had harnessed the demand for steam power by producing rolled iron plate for steam engines. Lukens continued this line of production and propelled Brandywine to become the leading producer of boilerplate. But she saw another opportunity for iron when the Philadelphia & Columbia Railroad, one of the first commercial railways in the U.S., launched in the mid-1830s, and she began seeking out commissions to produce iron for locomotives.

Even in the midst of the financial crisis of the Great Panic of 1837, Brandywine continued to roll out iron, and when business was stagnant, she sustained her employees by putting them to work maintaining and updating the mill. When she couldn’t pay them with money, she paid them with food. Her foresight and willingness to seek out new opportunities kept Brandywine afloat when other ironworks failed, and her business emerged from the Panic as the most prominent ironworks company. Lukens herself is remembered as the first woman CEO of an industrial company, and one of the first female ironmasters in the US.

3. Elizabeth Hobbs Keckley

A drawing of Elizabeth Hobbs Keckley from her book
A drawing of Elizabeth Hobbs Keckley from her book
Behind the Scenes by Elizabeth Hobbs Keckley, HathiTrust // Public Domain

Elizabeth Hobbs Keckley was one of Washington, D.C.'s most popular 19th century dressmakers—but it was a long and difficult road to financial independence and recognition. Born into slavery in Virginia in 1818, Keckley was moved from plantation to plantation. Taught sewing by her seamstress mother Agnes Hobbs, Keckley used this skill while still a teenager to build a clientele, making dresses for both white women and freed black women. While much of the money that she made from her dresses went to the family who owned her, some of her loyal clients loaned her the $1200 she needed to buy her and her son’s freedom. Keckley worked to pay back all the patrons who helped her buy her freedom before moving to Washington, D.C.

In D.C., word of her talents reached Mary Todd Lincoln. The first lady took Keckley on as her personal designer—and close personal friend. Keckley designed nearly all of Mary’s gowns during her time in the White House, including the dress she wore at Lincoln’s second inauguration, now on display at the Smithsonian. As a visible and well-respected free black woman, Keckley also founded the Contraband Relief Association (later the Ladies’ Freedmen and Soldiers’ Relief Association), an organization that raised money and provided food and clothing for black people and wounded Union soldiers.

Keckley’s success in D.C. ended, however, shortly after she published an 1868 autobiography—Behind the Scenes, Or, Thirty Years a Slave and Four Years in the White House. Mary saw the sections about her and the White House as a betrayal of confidence, and ended their friendship. The ripple effects ruined Keckley’s reputation in D.C. In the aftermath, she was offered a position at Wilberforce University in Ohio as head of the Department of Sewing and Domestic Science Arts, which she accepted. Keckley also organized the dress exhibit at the 1893 Chicago World’s Fair. She died in 1907.

4. Lydia Estes Pinkham

An advertising postcard for Lydia E. Pinkham
An advertising postcard for Lydia E. Pinkham
Boston Public Library // No known copyright restrictions

Lydia Pinkham reputedly came into possession of a secret medicinal recipe when her husband Isaac accepted the formula in lieu of money owed to him. The recipe contained five main herbs—pleurisy root, life root, fenugreek, unicorn root, and black cohosh—and alcohol. Pinkhman brewed her first batch of the soon-to-be-famous Vegetable Compound on her stove, and just three years later, she launched the Lydia E. Pinkham Medicine Co., a home remedy business run by and for women.

Pinkham claimed that her Vegetable Compound could cure a spectrum of female-specific ailments, from menstrual problems to a prolapsed uterus. She started out small, first distributing her compound to neighbors and friends, but in the midst of the financial crisis of 1873—when her husband was ruined—she began selling it and writing female health pamphlets to go alongside it. Her three sons helped her package, market, and sell the compound, and the strategic advertising campaign they implemented was key to the business’s success. She was the first woman to put her own likeness on her product, which helped create brand loyalty and spoke to her target audience: women. Eventually, she was able to expand her business beyond the U.S. and into Canada and Mexico.

There is little evidence proving the medical efficacy of Pinkham’s Vegetable Compound, and she is often lumped into the quackery category along with hundreds of other 19th century patent medicine producers. But she was also addressing a need for women-centered health care, which was often inadequate at the time. To find alternative methods of care, and avoid dangerous, expensive doctor visits, women often turned to home remedies—like Pinkham’s compound.

5. Madam C.J. Walker

Tin for Madame C.J. Walker's Wonderful Hair Grower
Tin for Madame C.J. Walker's Wonderful Hair Grower

Born Sarah Breedlove on a Louisiana plantation on December 23, 1867, Walker was the daughter of Owen and Minerva Anderson, freed blacks who both died by the time she was 7. She was married at 14, and soon gave birth to one daughter, Lelia. After her husband died only six years into their marriage, Walker moved to St. Louis, where she worked hard as a laundress and cook, hoping to provide a life free from poverty for Lelia.

In 1904, Walker began working as a sales agent for Annie Turnbo Malone’s hair care company—and soon came into some inspiration of her own. As the story goes, she had a dream in which a man told her the ingredients for a hair-growing tonic. Walker re-created the tonic and began selling it door-to-door. After she married Charles Joseph Walker in 1906 and renamed herself Madam C.J. Walker, she launched Madam Walker’s Wonderful Hair Grower, a line of hair care for black women.

Walker built a business that was earning $500,000 a year by the time she died, while her individual financial worth reached $1 million. Yet it isn’t the wealth alone that earned Walker a lasting legacy—it was how she used that wealth for a larger social good. Within her company, she trained over 40,000 black women and men and advocated for the economic independence of black people, particularly black women. She financially supported black students at the Tuskegee Institute, and contributed the largest recorded single donation, of $5000, to the NAACP, to support anti-lynching initiatives.

6. Annie Turnbo Malone

Though Madam C.J. Walker is often recognized as the first black woman millionaire, some historians say that credit belongs to Annie Turnbo Malone, the woman who hired Walker to sell her Wonderful Hair Grower in St. Louis before Walker started her own company. Like Walker, Malone’s parents were former slaves who died when Malone was young. Her older sister Peoria raised her, and together, they began experimenting with hairdressing.

Hair care products for black women were not widely produced, and the chemical solutions that were used often damaged hair. Malone developed her own chemical straightener around the turn of the century, and soon had created an entire line of other products for black women’s hair. In 1902 later, she moved to St. Louis and, along with three assistants, sold her hair care line door-to-door. She expanded the company rapidly, advertising in newspapers, traveling to give demonstrations at black churches, and even selling her line at the 1904 World’s Fair. In 1906, Malone trademarked her products under the name Poro, and in 1918, she built Poro College, a multi-story building that housed her business offices, training offices, operations, and a variety of public gathering spaces for the local black community. Malone even franchised retail outlets throughout North and South America, Africa, and the Philippines, employing over 75,000 women worldwide.

Malone’s company was worth millions, and she continuously used her money to improve the lives of those around her, either by hiring women or donating to colleges and organizations around the country. She made $25,000 donations to both Howard University Medical School and the St. Louis Colored YMCA. She donated the land for the St. Louis Colored Orphans’ Home and raised most of their construction costs, then served on their board from 1919 to 1943. In 1946, the orphanage was renamed in her honor, and it is still operational today as the Annie Malone Children and Family Service Center.

7. Mary Ellen Pleasant

When Mary Ellen Pleasant moved to San Francisco in 1852 she was fleeing the South, where she had been accused of violating the Fugitive Slave Law of 1850. Pleasant had, in fact, broken the law—which punished anyone who aided people escaping slavery—as a member of the Underground Railroad, along with her first husband James Smith. For four years, Pleasant and Smith helped escaped slaves find new homes in free states and Canada, and when Smith died only four years after their marriage, Pleasant continued the work with a considerable inheritance from him.

When Pleasant moved to San Francisco in 1852 amid Gold Rush fever, she initially worked as a cook and housekeeper, but also began investing in stock and money markets, and lending money to miners and other businessmen in California's surging economy (at interest, of course). Pleasant was successful enough that she became a philanthropist, and continued her abolitionist work by housing escaped slaves and finding them jobs.

In 1866, Pleasant brought a civil rights case against the North Beach Mission Railroad Company, which refused to pick up black passengers. She won. Her success in court, as well as in continuing the Underground Railroad through her businesses, have earned her the title the mother of California’s civil rights movement.

By this time, Pleasant had amassed a sizable fortune and was considered one of the wealthiest women in America. But many people in white society saw her only as a black stereotype, and dubbed her Mammy Pleasant—a title she hated. She ended up being dragged into a series of scandals and court cases connected to wealthy men, accused of being both a thief and murderer. Financially drained and emotionally exhausted, she was forced to give up her home. The smear campaigns also greatly diminished her fortune and reputation in her time, but the legacy of her radical life has not been lost. In 2005, the city of San Francisco proclaimed February 10 Mary Ellen Pleasant Day in her honor.

8. Olive Ann Beech

A photograph of Olive Ann Beach
A photograph of Olive Ann Beach
San Diego Air and Space Museum Archive, Wikimedia // No known restrictions

From an early age, Beech knew how to manage finances. Born in 1903, she had her own bank account by the age of 7, and by 11 she had taken on the unusual childhood responsibility of keeping track of her family’s accounts. Already with a mind for business and finance, Beech enrolled in a business college in her home state of Kansas, where she studied stenography and bookkeeping. After college, she took a position in 1924 as a bookkeeper for Travel Air Manufacturing Company, a new commercial and passenger aviation company.

Beech was fundamental to the company’s growth, managing its correspondence, records, and financial dealings, and the organization quickly became the world’s largest commercial aircraft manufacturer. In a short time, she was promoted to office manager, and eventually became personal secretary to Walter Beech, one of Travel Air’s co-founders. Their working relationship became much more, and they married in 1930. As partners, they formed Beech Aircraft Company, and when Walter fell sick for a few months, Beech took over. With the onset of the U.S.’s entry into World War II, Beech Aircraft boomed, building over 7400 military aircraft over the course of the war.

When Walter died in 1950, Beech became president—the first woman president of a major aircraft company. She then took the company into the Space Age, establishing a research and development facility that supplied NASA with cryogenic systems, cabin pressurizing equipment for the Gemini program, and parts for the Apollo moon flights and Orbiter shuttle. Under Beech’s leadership, the company’s sales tripled.

In 1980, Beech Aircraft merged with Raytheon; Beech stayed on as chair of Beech Aircraft and was elected to Raytheon’s board of directors. Though Beech never piloted an aircraft herself, she was awarded the Wright Brothers Memorial Trophy that same year—the first woman to receive the award—for "five decades of outstanding leadership in the development of general aviation."

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